Seedling growth dynamics of Quercus macrocarpa Michx. and Quercus muhlenbergii Engelm. were compared over a 3-month period under optimal growth conditions. These two species are the dominant trees at the western limit of the eastern deciduous forest, and are typically confined to gallery forests along stream beds in tallgrass prairie. Since tallgrass prairie is characterized by a highly variable climate and is prone to periodic drought, we hypothesized that these oaks would have rapid root growth and produce deep taproots as seedlings, enabling them to avoid drought stress and persist in this region. These traits may also facilitate forest expansion into the more xeric tallgrass prairie if fires are suppressed. Taproots of Q. macrocarpa and Q. muhlenbergii grew to approximately 140 cm and 100 cm in length, respectively, after 104 days. In both species, 65% or more of seedling biomass was allocated below ground, and root/total biomass was significantly greater in Q. muhlenbergii at 0–20 and 21–40 days after germination. The seedling taproot elongation rates reported here are much greater than rates reported in other eastern deciduous forest trees. Long-term precipitation data and soil moisture patterns from tallgrass prairie, when combined with rapid taproot elongation rates, suggest that soil moisture may not limit oak establishment or growth in tallgrass prairie in most years, although water uptake by roots was not measured in this study. Other factors, such as fire, herbivory, and seed predation and dispersal may be equally important in constraining the distribution of these species to gallery forests.